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Chemical Structure| 19130-96-2
Chemical Structure| 19130-96-2
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Product Details of [ 19130-96-2 ]

CAS No. :19130-96-2 MDL No. :MFCD00063474
Formula : C6H13NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :LXBIFEVIBLOUGU-JGWLITMVSA-N
M.W : 163.17 Pubchem ID :29435
Synonyms :
Duvoglustat;BAY-h-5955;Moranoline;1-dNM;1-DNJ;D-1-Deoxynojirimycin;moranolin

Safety of [ 19130-96-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19130-96-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 19130-96-2 ]

[ 19130-96-2 ] Synthesis Path-Downstream   1~52

  • 2
  • [ 19130-96-2 ]
  • [ 100-39-0 ]
  • [ 72458-46-9 ]
YieldReaction ConditionsOperation in experiment
50% In water; acetonitrile
With potassium carbonate In N,N-dimethyl-formamide for 2h;
1.14 g With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;
  • 4
  • [ 69567-11-9 ]
  • [ 19130-96-2 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; water; for 14h; To a solution of per-O-benzyl-1-deoxynojirimycin 9 (1.1 g, 2.1 mmol) in dry MeOH (45 mL) was added 20% Pd(OH)2/C (0.15 g), and the suspension was acidified with 2 M aq. HCl, and then stirred under a H2 atmosphere for 14 h. The mixture was then filtered through a Celite pad and the filtrate was concentrated in vacuo to give crude DNJ 1 (0.54 g). Compound 1 was dissolved in dry DMF (5.5 mL), and to the corresponding solution, 1-azido-5-iodopentane (0.66 g, 2.76 mmol) and K2CO3 (0.88 g, 6.4 mmol) were added, and stirred at 80 C for 4.5 h. After that, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (4:1 ? 7:3 EtOAc-MeOH with 1% NH4OH) to afford 13 (0.26 g, 45% over two steps).
93% Step-3: Synthesis of Compound 5 (0129) (0130) A solution of 4 (1.06 g, 1.91 mmol) in EtOH (50 mL) was acidified to pH 2 with 1M aq HCl and purged of oxygen by bubbling argon through the solution for 15 minutes. Pd/C (10 wt %, 100 mg) was added and the mixture was exposed to 4 bar of hydrogen for 20 hours. The reaction mixture was filtered over a glass microfiber filter and the filter cake was rinsed successively with MeOH (4×20 mL) and H2O (2×20 mL). The combined filtrate was concentrated and coevaporated with MeOH (3×50 mL). The residue was purified by column chromatography with aluminum oxide (isocratic 16:3.7:0.3, n-propanol:H2O:NH4OH) to provide 5 (290 mg, 1.78 mmol) in 93% yield as a white foam.
93% With palladium 10% on activated carbon; hydrogen; In ethanol; water; under 3000.3 Torr; for 20h;pH 2; 4 solution (1.06 grams, 1.91 mmol)Acidified to pH ~ 2 with (50 mil) 1 M aqueous HCl in EtOH,Oxygen was purged by bubbling argon through the solution for 15 minutes.Of Pd / C (10 wt%, 100 mg) was added,The mixture was exposed to 4 bar of hydrogen for 20 hours.The reaction mixture was filtered through a glass microfiber filter,The filter cake was washed sequentially with MeOH (4 × 20 ml) and H 2 0 (2 × 20 ml).The combined filtrate was concentrated,Co-evaporated with MeOH (3 x 50 milliliters).The residue was purified by column chromatography on aluminum oxide (: 3.7: 16 isochlor 0.3,N-propanol: H 2 0: NH 4 OH) to give 5 (290 mg, 1.78 mmol) in 93% yield as a white foam.
85% With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water; at 20℃; A mixture of 8R (500 mg, 0.95 mmol) and 10% Pd/C (50 mg) inEtOH was acidified with conc. HCl (1 mL) and stirred the mixturefor 24-28 hours under H2. After completion of reaction as indicatedby TLC, the mixture was filtered over celite and concentrated. Flashchromatography using gradient elution (ethyl acetate/methanol5:1, v/v) afforded 9 as an amorphous solid: Yield 0.128 g, 85%

  • 6
  • [ 19130-96-2 ]
  • 6-propyloxy-1-hexanal [ No CAS ]
  • [ 160632-05-3 ]
YieldReaction ConditionsOperation in experiment
2c Synthesis of N-7-Oxadecyl-DNJTable 4. Materials for Synthesis of N-7-Oxadecyl-DNJ 6-Propyloxy- 1 -hexanal 585 mgPd/C 125 mgEthanol 15 mLAcetic acid mLProcedure: a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (15 mL), 6-propyloxy-l -hexanal (585 mg), and acetic acid (0. ImL) t room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-40%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product. (Lot: D- 1029-052 (840 mg). Completion of the reaction was monitored by thin layer chromatography (TLC); (eluent: 50% methanol in dichloromethane).
840 mg 2c Synthesis of N-7-Oxadecyl-DNJ Procedure: a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (15 mL), 6-propyloxy-1-hexanal (585 mg), and acetic acid (0.1 mL) t room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-40%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product. (Lot: D-1029-052 (840 mg). Completion of the reaction was monitored by thin layer chromatography (TLC); (eluent: 50% methanol in dichloromethane).
Procedure: a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (15 mL), 6-propyloxy-l-hexanal (585 mg), and acetic acid (0. lmL) t room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-40%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product. (Lot: D- 1029-052 (840 mg). Completion of the reaction was monitored by thin layer chromatography (TLC); (eluent: 50% methanol in dichloromethane).
2c Synthesis of N-7-Oxadecyl-DNJTable 4. Materials for Synthesis of N-7-Oxadecyl-DNJ 6-Propyloxy- 1 -hexanal 585 mgPd/C 125 mgEthanol 15 mLAcetic acid mLProcedure: a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (15 mL), 6-propyloxy-l -hexanal (585 mg), and acetic acid (0. ImL) t room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-40%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product. (Lot: D- 1029-052 (840 mg). Completion of the reaction was monitored by thin layer chromatography (TLC); (eluent: 50% methanol in dichloromethane).

  • 7
  • [ 109-65-9 ]
  • [ 19130-96-2 ]
  • [ 72599-27-0 ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 90℃; for 24h; To a suspension of 1b (0.1 g, 0.61 mmol) and potassium carbonate (0.34 g, 2.4 mmol) in DMF (1.0 mL) was added 1-bromobutane (0.2 g, 2.4 mmol) and stirred at 80-90 C for 24 h. Reaction mass pH was adjusted to acidic side with acetic acid and subsequently passed through acidic resin followed by treatment with 1-5% aqueous ammonia solution. Aqueous ammonical solution was concentrated completely to get miglustat (3) (0.108 g, 76%); 1H NMR (400 MHz, D2O): delta 3.95 (d, J = 2.2 Hz, 2H), 3.64 (dd, J = 3.8, 9.7 Hz, 1H), 3.50 (t, J = 9.5 Hz, 1H), 3.36 (t, J = 9.6 Hz, 1H), 3.28 (m, 1H), 2.9-3.06 (m, 2H), 2.7-2.8 (m, 2H), 1.54-1.64 (m, 2H), 1.3-1.39 (m, 2H), 0.91 (t, J = 7.3 Hz, 3H); 13C NMR (100 MHz, D2O): delta 80.0, 71.5, 70.4, 68.0, 58.6, 57.0, 55.0, 27.6, 22.5, 15.8; Mass (M+H)+ 220.20.
  • 8
  • [ 19130-96-2 ]
  • [ 7493-95-0 ]
  • 6-O-(α-D-galactopyranosyl)-1-deoxynojirimycin [ No CAS ]
  • 9
  • [ 72458-46-9 ]
  • [ 19130-96-2 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogen In ethanol
  • 10
  • [ 19130-96-2 ]
  • [ 638-66-4 ]
  • N-stearyl-1-deoxynojirimycin [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen In ethanol; ethyl acetate at 20℃; for 4h;
  • 11
  • [ 19130-96-2 ]
  • [ 540-51-2 ]
  • [ 72432-03-2 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 100℃; To a suspension of 1b (0.1 g, 0.61 mmol) and potassium carbonate (0.34 g, 2.4 mmol) in DMF (1.0 mL) was added bromoethanol (0.30 g, 2.4 mmol) and stirred at 90-100 C for 4-5 h. After completion of the reaction, reaction mass pH was adjusted to acidic (pH ?5) using acetic acid. Reaction mass was next passed through acidic resin and subsequently treated with 1-5% aqueous ammonia solution. Aqueous ammonical solution was concentrated completely to get crude miglitol (2) which was re-crystallized using methanol to afford white solid (0.1 g, 80%). White solid; [alpha]D20:-7.95 (c 0.56, H2O); M.P.=145.17C. IR (thin film) cm-1: 3365, 3280, 2922, 1545, 1429, 1304, 1075, 1033; 1H NMR (400MHz, D2O): delta 3.9 (dd, J=2.5,13.5Hz, 1H), 3.79 (dd, J=3.4, 12.9Hz, 1H), 3.7 (td, J=2, 6.4Hz, 2H), 3.49 (ddd, J=4.9, 3.4, 4.4Hz, 1H), 3.22-3.32 (m, 2H), 3.05 (dd, J=4.9, 11.3Hz, 1H), 2.90 (dt, J=6.8, 14.2Hz, 1H), 2.68 (dt, J=6.8, 14.2Hz, 1H), 2.29 (m, 2H); 13C NMR (100MHz, D2O): delta 81.1, 72.7, 71.5, 68.4, 60.7, 60.4, 58.9, 55.6; HRMS: calculated for C8H18NO5 [M+H]+ 208.1185, found 208.1194.
  • 12
  • [ 19130-96-2 ]
  • [ 693-58-3 ]
  • (2R,3R,4R,5S)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h;Microwave irradiation; 0.2 mmol of DNJ, 0.4 mmol of bromononane and 0.42 mmol of K2CO were added to a microwave synthesizer (Anton Paar, Monowave 100), 1 ml of dimethylformamide (DMF) was added thereto, The reaction was heated at 100 C for 3 hours using a microwave. After the reaction was completed, the reaction was filtered through celite and extracted three times with 5 mL of methanol (MeOH). The filtrate obtained after the extraction was reduced in pressure and subjected to column chromatography (MeOH: MC = 10: 90) to obtain 52 mg (yield 90%) of NN-DNJ in a white solid state.
  • 13
  • [ 19130-96-2 ]
  • [ 6621-59-6 ]
  • [ 885484-34-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In N,N-dimethyl-formamide; at 40℃; for 72h; Step a: A 3% solution of the respective iminoalditol in dry DMF was stirred with omega-bromohexanoic nitrile (2 equiv.) in the presence OfNa2CO3 (1.3 equiv.) at 40 0C for 72 h. Removal of the solvent and chromatographic purification (CHClj/MeOH 1 :1) gave the respective reaction products in yields ranging between 45 and 90 %.
  • 14
  • [ 19130-96-2 ]
  • [ 958880-39-2 ]
  • (2R,3R,4R,5S)-1-(6-((4-azido-2-nitrophenyl)amino)hexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sodium cyanoborohydride; acetic acid; In methanol; at 20℃; for 14h; EXAMPLE 1Synthesis of N-(N'-{4'azido-2'-nitrophenyl)-6-aminohexyl)-DNJ (NAP-DNJ). Direct displacement of the aromatic fluorine in 4-fluor-3-nitrophenyl azide (FNAP) by 6-aminohexanol produces the desired alcohol which is oxidized to the aldehyde. The resulting aldehyde is subjected to reductive amination with DNJ to produce the final product as shown in Scheme II. Characterization of the NAP-DNJ was conducted using 1H and 13C NMR and mass spectrometry. The results from 1D (1H and 13C) NMR are tabulated in Table 1, and the COSY and NOESY results are shown below. 1H NMR are arbitrary and 13C NMR are referenced to methanol (49.0 ppm). TABLE 1 1H NMR (500 mHz)13C NMR Atom delta (ppm) mult3JHH (Hz) delta (ppm) mult1JCH (Hz) C1 2.878 dd 11.2/4.9 57.7 2.054 dd 11.2/10.4 C2 3.352 ddd 4.9/10.4/9.2 70.8 C3 3.013 dd 9.2/9.1 80.6 C4 3.227 dd 9.1/9.6 72.1 C5 2.004 ddd 9.6/2.7/2.7 67.5 C6 3.753 dd 11.9/2.7 59.6 3.711 dd 11.9/2.7 C7 2.703 ddd 53.7 2.461 ddd C8 1.42 o/i 25.3 C9 1.260 m 28.2 C10 1.38 o/i 27.9 C11 1.615 m 30.0 C12 3.258 t 43.9 C13 - - 128.8 C14 - - 132.5 C15 7.668 d 2.7 116.5 C16 - - 144.7 C17 7.137 dd 2.7/9.2 129.3 C18 6.965 d 9.2 117.3 1H-1H COSY experiment: C1H/H'-C2H-C3H-C4H-C5H-C6H/H'; C7H/H'-C8H2-C9H2-C10H2-C11H2-C12H2; C15H-C17H-C18H. The aromatic ring is therefore 1,2,4-substituted and the C7 is attached, or part of a rigid ring.NOESY experiment (400 msec): C7H?C1H (138), C6H/H' (343); C7H'?C6H/H' (325); C12H2?C18H. The large coupling constants around the ring suggest that C1H', C2H, C3H, C4H and C5H are all trans di-axial. This indicates that the ring has glucose stereochemistry, i.e., is DNJ. The NOES from C7H/H' to C1H/H' and C6H/H' indicates that C12 is linked to the aromatic ring and probably in a ring position ortho to C18.Spectroscopy: [alpha]D22-7.7 (c 0.026, MeOH); vmax (Ge) 3356 (NH+OH), 2926, 2856 (CH), 2119 (N3), 1633, 1556 (CC), 1521, 1347 (NO2) cm-1. Mass spectrometry: m/z (ES+): 425.33 ([M+H]+, 100%); HRMS (ES+): Found 425.2152 ([M+H]+) required 426.2149.
  • 15
  • [ 19130-96-2 ]
  • [ 123-72-8 ]
  • [ 72599-27-0 ]
YieldReaction ConditionsOperation in experiment
palladium; In methanol; EXAMPLE 1 Preparation of 1,5-(butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29C/21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone, and recrystallized from methanol/acetone, m.p. ca. 132C. The structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10H21NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; EXAMPLE 1 Preparation of 1,5-(Butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29C/21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone, and recrystallized from methanol/acetone, m.p. ca. 132C. The structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10H21NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; EXAMPLE 6 STR6 1,5-(Butylimino)-1,5-dideoxy-D-glucitol. A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone and recrystallized from methanol/acetone, m.p. ca. 132 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10 H21 NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; EXAMPLE 6 STR6 1,5-(Butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone and recrystallized from methanol/acetone, m.p. ca. 132 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10 H21 NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; Example 6 1,5-(Butylimino) -1,5-dideoxy-D-glucitol STR10 A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone and recrystallized from methanol/acetone, m.p. ca. 132 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10 H21 NO4: H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
With hydrogenchloride; sodium cyanoborohydride; In methanol; at 0 - 20℃; for 12h; II. NB-DNJ: 12.5 ml of n-butyraldehyde, 0.01 mols of methanol.c HCl and 1.5 g of NaCNBH3 are added successively to 3.2 g of 1-deoxynojirimycin (0.02 mol) in 40 ml of absolute methanol, while cooling with ice and stirring. The reaction mixture is stirred at room temperature for 12 hours. It is then concentrated to dryness on a rotary evaporator. The residue is dissolved in 50 ml of water and extracted 3 times with 30 ml of CHCl3 each time. The aqueous phase is again brought to dryness, the residue is taken up in 30 ml of H2O and the solution is discharged onto a column 50 cm long and 2 cm wide which is filled with a strongly basic ion exchange resin in the OHphi form (Amberlite IRA 400 or Dowex 1X2) . EPO <DP n="49"/>The reaction product is eluted with water and the individual fractions are investigated by thin layer chromatography. (Silica gel plates; running agent: ethyl acetate/methanol/water/25% strength ammonia 100:60:40:2; spray reagent: KMnO4 solution) . The fractions which contain N-n-butyl-1-desoxynojirimycin are collected and the aqueous solution is concentrated on a rotary evaporator. Acetone is added to the residue, whereupon crystallization occurs.The crystals are filtered off, rinsed briefly with acetone and dried. 3 g of N-n-butyl-1-desoxynojirimycin of melting point 126- 127 C. are obtained.Mass spectrum: The most important peaks in the upper mass range are found at m/e=188 (M--CH2 OH) and m/e=176 (M- CH2 - CH2 - CH3) .In the case of less reactive aldehydes, a molecular sieve 3 A is added to the reaction mixture in order to bind the water of reaction.
palladium; In methanol; EXAMPLE 6 STR7 1,5-(Butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone and recrystallized from methanol/acetone, m.p. ca. 132 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10 H21 NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; EXAMPLE 6 STR6 1,5-(Butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone and recrystallized from methanol/acetone, m.p. ca. 132 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10 H21 NO4 L: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; EXAMPLE 1 Preparation of 1,5-(butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol is hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate is concentrated in vacuo to an oil. The title compound is crystallized from acetone, and recrystallized from methanol/acetone, m.p. ca. 132 C. The structure assignment is supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10H21NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
Pd black; In methanol; EXAMPLE 1 Preparation of 1,5-(butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone, and recrystallized from methanol/acetone, m.p. ca. 132 C. The structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10H21NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.
palladium; In methanol; EXAMPLE 1 Preparation of 1,5-(butylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (5.14 g, 0.0315 mole), butyraldehyde (3.35 ml, 0.0380 mole) and Pd black (1 g) in 200 ml methanol was hydrogenated (60 psi/29 C./21 hrs.). After filtering the resulting mixture, the filtrate was concentrated in vacuo to an oil. The title compound was crystallized from acetone, and recrystallized from methanol/acetone, m.p. ca. 132 C. The structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C10H21NO4: C, 54.78; H, 9.65; N, 6.39. Found: C, 54.46; H, 9.33; N, 6.46.

  • 16
  • [ 124-19-6 ]
  • [ 19130-96-2 ]
  • (2R,3R,4R,5S)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
palladium; In methanol; EXAMPLE 13 STR13 1,5-(Nonylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (0.5 g, 0.0031 mole); nonyl aldehyde (0.52 g, 0.0037 mole) and 5% Pd black (0.1 g) in methanol (100 ml) was hydrogenated (60 psi/25 C./46 hrs.). After filtering the resulting mixture, the filtrate was concentrated with a gentle flow of nitrogen to an oily solid. This material was stirred with a small amount of acetone and the solid filtered. Recrystallization from ethanol--acetone gave the title compound, DSC ca. 109 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C15 H31 NO4: C, 62.25; H, 10.80; N, 4.84. Found: C, 62.15; H, 10.86; N, 4.79.
palladium; In methanol; EXAMPLE 13 STR13 1,5-(Nonylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (0.5 g, 0.0031 mole), nonyl aldehyde (0.52 g, 0.0037 mole) and 5% Pd black (0.1 g) in methanol (100 ml) was hydrogenated (60 psi/25 C./46 hrs.). After filtering the resulting mixture, the filtrate was concentrated with a gentle flow of nitrogen to an oily solid. The material was stirred with a small amount of acetone and the solid filtered. Recrystallization from ethanol-acetone gave the title compound, DSC ca. 109 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C15 H31 NO4: C, 62.25; H, 10.80; N, 4.84. Found: C, 62.15; H, 10.86; N, 4.79.
palladium; In methanol; EXAMPLE 13 STR14 1,5-(Nonylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (0.5 g, 0.0031 mole); nonyl aldehyde (0.52 g, 0.0037 mole) and 5% Pd black (0.1 g) in methanol (100 ml) was hydrogenated (60 psi/25 C./46 hrs.). After filtering the resulting mixture, the filtrate was concentrated with a gentle flow of nitrogen to an oily solid. This material was stirred with a small amount of acetone and the solid filtered. Recrystallization from ethanol-acetone gave the title compound, DSC ca. 109 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C15 H31 NO4: C, 62.25; H, 10.80; N, 4.84. Found: C, 62.15; H, 10.86; N, 4.79.
palladium; In methanol; EXAMPLE 3 1,5(Nonylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (0.5 g, 0.0031 mole), nonyl aldehyde (0.52 g, 0.0037 mole) and 5% Pd black (0.1 g) in methanol (100 ml) was hydrogenated (60 psi/25 C./46 hrs.). After filtering the resulting mixture, the filtrate was concentrated with a gentle flow of nitrogen to an oily solid. This material was stirred with a small amount of acetone and the solid filtered by reduced pressure. Recrystallization from ethanol-acetone gave the title compound, DSC ca. 109 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis (289.4). Analysis calcd. for C15 H31 NO4: C, 62.25; H, 10.80; N, 4.84. Found: C, 62.15; H, 10.86; N, 4.79.
palladium; In methanol; EXAMPLE 13 STR13 1,5-(Nonylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (0.5 g, 0.0031 mole); nonyl aldehyde (0.52 g, 0.0037 mole) and 5% Pd black (0.1 g) in methanol (100 ml) was hydrogenated (60 psi/25 C./46 hrs.). After filtering the resulting mixture, the filtrate was concentrated with a gentle flow of nitrogen to an oily solid. This material was stirred with a small amount of acetone and the solid filtered. Recrystallization from ethanol - acetone gave the title compound, DSC ca. 109 C. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C15 H31 NO4: C, 62.25; H, 10.80; N, 4.84. Found: C, 62.15; H, 10.86; N, 4.79.
Working Examples 1. Synthesis of N-Nonyl DNJTable 1. Materials for NN-DNJ synthesisProcedure: A 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (100 mL), nonanal (530 mg), and acetic acid (0.5 mL ) at room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-25%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product (420mg). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent; methanol : dichloromethane = 1 :2
420 mg 1. Synthesis of N-Nonyl DNJ [tabl0001-en] Table 1. Materials for NN-DNJ synthesisName Amount DNJ 500 mg Nonanal 530 mg Ethanol 100 mL AcOH 0.5 mL Pd/C 500 mg (0042) Procedure: A 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (100 mL), nonanal (530 mg), and acetic acid (0.5 mL) at room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-25%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product (420mg). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent; methanol: dichloromethane = 1:2
Procedure: A 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (100 mL), nonanal (530 mg), and acetic acid (0.5 mL ) at room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-25%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product (420mg). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent; methanol : dichloromethane = 1 :2
Working Examples 1. Synthesis of N-Nonyl DNJTable 1. Materials for NN-DNJ synthesisProcedure: A 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with DNJ (500 mg), ethanol (100 mL), nonanal (530 mg), and acetic acid (0.5 mL ) at room temperature. The reaction mixture was heated to 40-45 C and stirred for 30-40 minutes under nitrogen. The reaction mixture was cooled to ambient temperature and Pd/C was added. The reaction flask was evacuated and replaced by hydrogen gas in a balloon. This process was repeated three times. Finally, the reaction mixture was stirred at ambient temperature overnight. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography (230-400 mesh silica gel). A solvent gradient of methanol in dichloromethane (10-25%) was used to elute the product from the column. All fractions containing the desired product were combined, and concentrated in vacuo to give the pure product (420mg). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent; methanol : dichloromethane = 1 :2

  • 17
  • [ 19130-96-2 ]
  • [ 69567-10-8 ]
YieldReaction ConditionsOperation in experiment
With formaldehyd;palladium; In methanol; EXAMPLE 9 STR9 1,5-(Methylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (7.5 g, 0.046 mole), formaldehyde (37%, 26.0 g, 0.322 mole) and 5% Palladium black in 300 ml methanol was hydrogenated (60 psi/25 C./20 hrs). After filtering the resulting mixture, the filtrate was concentrated to give a foam. The product was crystallized from methanol-acetone to give a while solid. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C7 H15 NO4: C, 47.45; H, 8.53; N, 7.91. Found: C, 47.24; H, 8.66; N, 7.83.
With formaldehyd;palladium; In methanol; EXAMPLE 9 STR9 1,5-(Methylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (7.5 g, 0.046 mole), formaldehyde (37%, 26.0 g, 0.322 mole) and 5% Palladium black in 300 ml methanol was hydrogenated (60 psi/25 C./20 hrs.). After filtering the resulting mixture, the filtrate was concentrated to give a foam. The product was crystallized from methanol-acetone to give a white solid. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C7 H15 NO4: C, 47.45; H, 8.53; N, 7.91. Found: C, 47.24; H, 8.66; N, 7.83.
With formaldehyd;palladium; In methanol; Example 9 1,5-(Methylimino)-1,5-dideoxy-D-glucitol STR13 A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (7.5 g, 0.046 mole), formaldehyde (37%, 26.0 g, 0.322 mole) and 5% Palladium black in 300 ml methanol was hydrogenated (60 psi/25 C./20 hrs). After filtering the resulting mixture, the filtrate was concentrated to give a foam. The product was crystallized from methanol-acetone to give a white solid. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C7 H15 NO4, C 47.45; H, 8.53; N, 7.91. Found: C, 47.24; H, 8.66; N, 7.83.
With formaldehyd;palladium; In methanol; EXAMPLE 9 STR10 1,5-(Methylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (7.5 g, 0.046 mole), formaldehyde (37%, 26.0 g, 0.322 mole) and 5% Palladium black in 300 ml methanol was hydrogenated (60 psi/25 C./20 hrs). After filtering the resulting mixture, the filtrate was concentrated to give a foam. The product was crystallized from methanol-acetone to give a white solid. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C7 H15 NO4, C 47.45; H, 8.53; N, 7.91. Found: C, 47.24; H, 8.66; N, 7.83.
With formaldehyd;palladium; In methanol; EXAMPLE 9 STR9 1,5-(Methylimino)-1,5-dideoxy-D-glucitol A solution of <strong>[19130-96-2]1,5-dideoxy-1,5-imino-D-glucitol</strong> (7.5g, 0.046 mole), formaldehyde (37%, 26.0g, 0.322 mole) and 5% Palladium black in 300 ml methanol was hydrogenated (60 psi/25 C./20 hrs). After filtering the resulting mixture, the filtrate was concentrated to give a foam. The product was crystallized from methanol-acetone to give a white solid. Structure assignment was supported by NMR, infrared spectra and elemental analysis. Analysis calcd. for C7 H15 NO4: C, 47.45; H, 8.53; N, 7.91. Found: C, 47.24; H, 8.66; N, 7.83.

  • 18
  • [ 19130-96-2 ]
  • [ 406-81-5 ]
  • [ 128985-16-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N-methyl-acetamide; EXAMPLE 59 STR59 1,5-(4,4,4-Trifluorobutylimino)-1,5-dideoxy-D-glucitol A solution of 1,5-dideoxy-1,5-imino-D-glucitol (6.07 g, 0.0372 mole), 4,4,4-trifluoro-1-bromobutane (7.1 g, 0.0372 mole) and potassium carbonate (2.57 g, 0.0186 mole) was stirred in dimethylformamide (400 ml) for 37 days. The reaction was filtered and concentrated to an oil. The product was purified by silica gel chromatography and crystallized from ethyl acetate. The structure of the title compound was supported by NMR and elemental analysis (273.25). Analysis calcd. for C10 H18 NO4 F3: C, 43.96; H, 6.64; N, 5.13. Found: C, 43.89; H, 6.69; N, 4.73.
  • 19
  • [ 19130-96-2 ]
  • [ 75-07-0 ]
  • [ 72458-42-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium; In methanol; water; at 20 - 22℃; under 3102.97 Torr; for 20h; A mixture of 1-DNJ (1.0 g, 6.1 mmol), methanol (60 mL), DI water (3.0 mL), acetaldehyde (6.2 g, 141 mmol) and Pd black (50 mg) is rapidly stirred and hydrogenated at 20-22 C. under 60 psi pressure of H2 for 20 h. The catalyst removed by filtration through a bed of Celite-545. The filtrate is evaporated using a rotovap. The non-volatile residue is applied to a flash silica gel column and eluted with a mixture comprised of methylene chloride: methanol: 29% and conc. NH4OH (70:30:5). The appropriate fractions are collected, combined, evaporated using a rotovap. Lyophilized affords the desired isolated product. MP 168.3-169.6 C., m/z 192 (ES, [M+H]+).
  • 20
  • [ 19130-96-2 ]
  • [ 58257-19-5 ]
  • [ 615253-61-7 ]
YieldReaction ConditionsOperation in experiment
28.1% 3 c Synthesis of N-(9-methoxy)-nonyl DNJ Table 7. Materials for synthesis of N-(9-methoxy)-nonyl DNJProcedure: a 50-mL, two-necked, round-bottom flask equipped with magnetic stirrer and a stir bar was charged with DNJ (300 mg, 1.84 mmol), ethanol (20 mL), 9-methoxy- 1 -nonanal (476 mg, 2.76 mmol) at room temperature. The reaction mixture was stirred for 5-10 minutes under nitrogen and Pd/C was added at room temperature. The reaction mixture was evacuated and was replaced by hydrogen gas using a balloon. This process was repeated three times and then reaction mixture was stirred under atmospheric hydrogen at room temperature. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a bed of Celite and was washed with ethanol (20 mL). The filtrate was concentrated in vacuo to get a crude product. The crude product was purified by column chromatography using 250-400 mesh silica gel (20 g). A solvent gradient of methanol in ethyl acetate (5- 25%) was used to elute the product from the column. All fractions containing the desired pure product were combined, and concentrated in vacuo to give an off white solid. The solid was triturated in ethyl acetate (20 mL), filtered and dried in high vacuum to give a white solid [lot: D-1027-158 (165.3 mg, 28.1%). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 50% methanol indichloromethane .
28.1% 3c Synthesis of N-(9-methoxy)-nonyl DNJ [tabl0007-en] Table 7. Materials for synthesis of N-(9-methoxy)-nonyl DNJName Amount DNJ 300 mg 9-methoxy-1-nonanal 476 mg Pd/C 200 mg Ethanol 20 mL (0054) Procedure: a 50-mL, two-necked, round-bottom flask equipped with magnetic stirrer and a stir bar was charged with DNJ (300 mg, 1.84 mmol), ethanol (20 mL), 9-methoxy-1-nonanal (476 mg, 2.76 mmol) at room temperature. The reaction mixture was stirred for 5-10 minutes under nitrogen and Pd/C was added at room temperature. The reaction mixture was evacuated and was replaced by hydrogen gas using a balloon. This process was repeated three times and then reaction mixture was stirred under atmospheric hydrogen at room temperature. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a bed of Celite and was washed with ethanol (20 mL). The filtrate was concentrated in vacuo to get a crude product. The crude product was purified by column chromatography using 250-400 mesh silica gel (20 g). A solvent gradient of methanol in ethyl acetate (5-25%) was used to elute the product from the column. All fractions containing the desired pure product were combined, and concentrated in vacuo to give an off white solid. The solid was triturated in ethyl acetate (20 mL), filtered and dried in high vacuum to give a white solid [lot: D-1027-158 (165.3 mg, 28.1 %). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 50% methanol in dichloromethane.
28.1% Procedure: a 50-mL, two-necked, round-bottom flask equipped with magnetic stirrer and a stir bar was charged with DNJ (300 mg, 1.84 mmol), ethanol (20 mL), 9-methoxy- 1 -nonanal (476 mg, 2.76 mmol) at room temperature. The reaction mixture was stirred for 5-10 minutes under nitrogen and Pd/C was added at room temperature. The reaction mixture was evacuated and was replaced by hydrogen gas using a balloon. This process was repeated three times and then reaction mixture was stirred under atmospheric hydrogen at room temperature. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a bed of Celite and was washed with ethanol (20 mL). The filtrate was concentrated in vacuo to get a crude product. The crude product was purified by column chromatography using 250-400 mesh silica gel (20 g). A solvent gradient of methanol in ethyl acetate (5- 25%) was used to elute the product from the column. All fractions containing the desired pure product were combined, and concentrated in vacuo to give an off white solid. The solid was triturated in ethyl acetate (20 mL), filtered and dried in high vacuum to give a white solid [lot: D-1027-158 (165.3 mg, 28.1%). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 50% methanol indichloromethane .
28.1% 3 c Synthesis of N-(9-methoxy)-nonyl DNJ Table 7. Materials for synthesis of N-(9-methoxy)-nonyl DNJProcedure: a 50-mL, two-necked, round-bottom flask equipped with magnetic stirrer and a stir bar was charged with DNJ (300 mg, 1.84 mmol), ethanol (20 mL), 9-methoxy- 1 -nonanal (476 mg, 2.76 mmol) at room temperature. The reaction mixture was stirred for 5-10 minutes under nitrogen and Pd/C was added at room temperature. The reaction mixture was evacuated and was replaced by hydrogen gas using a balloon. This process was repeated three times and then reaction mixture was stirred under atmospheric hydrogen at room temperature. The progress of reaction was monitored by TLC (Note 1). The reaction mixture was filtered through a bed of Celite and was washed with ethanol (20 mL). The filtrate was concentrated in vacuo to get a crude product. The crude product was purified by column chromatography using 250-400 mesh silica gel (20 g). A solvent gradient of methanol in ethyl acetate (5- 25%) was used to elute the product from the column. All fractions containing the desired pure product were combined, and concentrated in vacuo to give an off white solid. The solid was triturated in ethyl acetate (20 mL), filtered and dried in high vacuum to give a white solid [lot: D-1027-158 (165.3 mg, 28.1%). Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 50% methanol indichloromethane .

  • 21
  • [ 149302-60-3 ]
  • [ 19130-96-2 ]
YieldReaction ConditionsOperation in experiment
91% With 10 wt% Pd(OH)2 on carbon; hydrogen; In ethanol; chloroform; at 20℃; for 20h; To a solution of 10 (614mg, 1 mmol) in EtOH (10 mL) and CHCl3 (2.5 mL) was added Pd(OH)2/C (10 wt% Pddry basis on carbon, 100 mg), and the mixture was hydrogenated at r.t. for 20h. The suspension was filteredthrough Celite pad. The filter cake was rinsed with EtOH. The combined filtrate and washings were concentratedin vacuo. Some CH2Cl2 was added to the residual oil, 8 was crystallized at once as a white solid, filtered throughCelite pad to give pure 1 (150 mg, 91%) .
  • 22
  • [ 19130-96-2 ]
  • [ 2277-19-2 ]
  • [ 1383153-17-0 ]
YieldReaction ConditionsOperation in experiment
75% With sodium cyanoborohydride; acetic acid In tetrahydrofuran; methanol at 20℃; for 24h; Inert atmosphere;
  • 23
  • [ 19130-96-2 ]
  • [ 2212-06-8 ]
  • [ 1225048-88-3 ]
YieldReaction ConditionsOperation in experiment
81% In methanol; water at 20℃; for 24h;
  • 24
  • [ 19130-96-2 ]
  • N-cyclohexyl-N-(6-oxohexyl)benzamide [ No CAS ]
  • [ 1447464-65-4 ]
YieldReaction ConditionsOperation in experiment
47% N-cyclohexyl-N-(6-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl) piperidin-1- yl)hexyl)benzamide: A solution of DNJ (47 mg, 0.29 mmol) in acetic acid (2 mL) was stirred at room temperature for an hour, and then the solvent was removed under reduced pressure. The resulting residue was treated with 200 proof ethanol (5 mL) and the aldehyde prepared above (108.2 mg, 0.36 mmol). Then, it was transferred to the hydrogenation bottle, followed by addition of 10% Pd/C (32 mg) and 200 proof ethanol (5 mL). The mixture was hydrogenated under 45 psi of H2 for 24 hours. After the reaction was complete, it was treated with celite (100 mg), and then filtered through a celite pad. The filtrate was concentrated and purified through silica gel column chromatography (methanol : ethyl acetate = 5: 95 to 15 : 85) to afford the product as a white solid (61 mg, 47%). 1H NMR (300 MHz, CD3OD): delta 7.50-7.42 (m, 3H), 7.37-7.29 (m, 2H), 3.94-2.75 (m, 2H), 3.58-3.30 (m,4H), 3.30-3.00 (m, 3H), 3.00-2.78 (m, 1H), 2.78-2.50 (m, 1H), 2.50-2.00 (m, 2H), 2.00- 1.20 (m, -0.80 (m, 3H). Calculated MS for ^Eta^NuLambda, 448.29; observed, 449.3.
  • 26
  • [ 19130-96-2 ]
  • [ 10527-16-9 ]
  • N-(10-chloro-9-anthracenemethyl)-1-deoxynojirimycin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1,5-dideoxy-1,5-imino-D-glucitol; 10-chloro-9-anthraldehyde With sodium cyanoborohydride In methanol; chloroform for 0.166667h; Reflux; Stage #2: With acetic acid In methanol; chloroform at 20 - 60℃; for 28h;
  • 27
  • [ 19130-96-2 ]
  • [ 76911-01-8 ]
  • C12H21NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 24h;Inert atmosphere; Potassium carbonate (1.23 mmol, 169 mg) wasadded to a solution of deoxynojirimycin 6 (0.613 mmol, 100 mg)and 5-hexyn-1-tosylate 5 (0.736 mmol, 186 mg) in DMF. The reactionmixture was heated to 80 C (in an oil bath) for 24 h under argon. Most of the DMF was evaporated under reduced pressure.1 N HCl was added to the residue, and the mixture was purifiedvia ion exchange chromatography (cation type DOWEX 50W), givingthe target compound, which was recrystallized from MeOH toafford 8 as white crystals (158 mg, 99%). 1H NMR (CD3OD): d 1.42(2H, m), 1.54 (2H, m), 2.03 (1H, J = 2.4, 9.6 Hz, dt), 2.14 (4H, m),2.51 (1H, m), 2.74 (1H, m), 2.91 (1H, J = 5.0, 11.0 Hz, dd), 3.06(1H, J = 8.4, 9.2 Hz, dd), 3.23 (2H, m), 3.27 (1H, J = 8.8, 10.0 Hz,dd), 3.39 (1H, J = 5.1, 9.2, 10.0 Hz, ddd), 3.78 (1H, J = 2.2, 12.0,21.0, 21.0 Hz, dddd). 13C NMR (CD3OD): d 17.6, 23.0, 26.2, 51.8,56.3, 58.1, 66.0, 68.4, 69.4, 70.7, 79.2, 83.5. ESI-HRMS calcd for C12-H21NNaO4: 266.1368; found 266.1343.
  • 28
  • [ 19130-96-2 ]
  • N-maleimido butane-4-carboxaldehyde [ No CAS ]
  • N-(4'-maleimidobutyl)-1-deoxynojirimycin [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% A solution of the aldehyde (M1973) (49 mg, 0.26 mmole) and 1-deoxynojirimycin (33 mg, 0.2 mmole) in anhydrous methanol (5 mL) containing glacial acetic acid (24 uL, 0.4 mmole) was allowed to stir at room temperature for 30 min. To this mixture was added 1 M sodium cyanoborohydride in anhydrous tetrahydrofuran (300 uL, 0.3 mmole) and the resulting reaction mixture allowed to stir under anhydrous conditions for 72 hours until t.l.c. analysis (irrigant=7:3 ethyl acetate:methanol) exhibited complete conversion of M1973 to a new product (Rf=0.2). Water (2.0 mL) was then added with stirring for 10 min. to destroy the excess borohydride, and the resulting solution evaporated and co-evaporated with methanol (3*5 ml) to a clear glass that was applied to a column of silicagel G (70-230 mesh, 25 g) slurry-packed in 3:1 ethyl acetate:methanol (120*25 mm) and eluted with 3:1 ethyl acetate:methanol (300 mL). Fractions containing the product were combined and evaporated to a clear oil (47 mg, 75%). 1H-NMR (d6-DMSO) delta: 1.34 (m, 2H); 1.40 (m, 2H); 2.30 (m, 1H); 2.74 (td, 2H); 2.90 (t, 1H); 2.98 (t, 1H); 3.15 (m, 1H); 3.36 (t, 1H); 3.50 (m, 1H); 3.71 (d, 1H); 4.11 (m, 1H); 4.67 (m, 3H); 7.00 (s, 2H, maleimide). T.l.c (irrigant=7:3 ethyl acetate:methanol, Rf=0.2).
  • 29
  • [ 19130-96-2 ]
  • [ 459-46-1 ]
  • C13H18FNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate; In N,N-dimethyl-formamide; K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%). 1H NMR (400 MHz, DMSO-d6) delta 7.35 (dd, J = 14.3, 7.5 Hz, 1H),7.16 (d, J = 6.0 Hz, 2H), 7.05 (t, J = 8.6 Hz, 1H), 4.78 (d, J = 5.3 Hz, 1H), 4.72 (d, J = 4.0 Hz, 1H), 4.62 (d,J = 4.3 Hz, 1H), 4.41 (s, 1H), 4.26 (d, J = 14.0 Hz, 1H), 3.94 (d, J = 11.6 Hz, 1H), 3.67-3.59 (m, 1H), 3.20-3.05 (m, 3H), 2.98-2.90 (m, 1H), 2.60 (dd, J = 11.1, 4.5 Hz, 1H), 2.03 (d, J = 8.4 Hz, 1H), 1.75 (t, J = 10.8Hz, 1H).13C NMR (100 MHz, DMSO-d6) delta 162.30, 159.89, 135.68, 130.51, 114.80, 114.59, 79.09, 70.91,69.14, 67.86, 59.79, 56.62, 55.56; HRMS: C13H18FNO4 for +, calculated 271.1215, found 271.1289; [alpha]24D -0.206 (0.53, DMSO).
  • 30
  • [ 19130-96-2 ]
  • [ 622-95-7 ]
  • C13H18ClNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 31
  • [ 19130-96-2 ]
  • [ 16004-15-2 ]
  • C13H18INO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 32
  • [ 19130-96-2 ]
  • [ 104-81-4 ]
  • (2R,3R,4R,5S)-2-Hydroxymethyl-1-(4-methyl-benzyl)-piperidine-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 33
  • [ 19130-96-2 ]
  • [ 2746-25-0 ]
  • C14H21NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 34
  • [ 19130-96-2 ]
  • [ 456-41-7 ]
  • C13H18FNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 35
  • [ 19130-96-2 ]
  • [ 49617-83-6 ]
  • C13H18INO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 36
  • [ 19130-96-2 ]
  • [ 620-13-3 ]
  • C14H21NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In N,N-dimethyl-formamide; General procedure: K2CO3 (4 mmol) was added to a solution of 1-DNJ (2 mmol) and 4-fluorobenzyl bromide (2.4mmol) in DMF. The mixture was stirred at r.t. until 1-DNJ was depleted, as determined by TLCanalysis. Then, the mixture was washed with EtOAc/H2O (v/v = 1:1). The aqueous phase was washed3 times with EtOAc. The combined extracts were washed successively with 1 M aq HCl and saturatedaq NaHCO3, dried over anhydrous Na2SO4, and evaporated by vacuum to obtain a residue. The residue was purified using silica gel column chromatography (dichloromethane: methyl alcohol =15:1) to produce a yellow solid (83%).
  • 37
  • [ 19130-96-2 ]
  • 28-(12-bromododecyl)maslinic acid ester [ No CAS ]
  • 28-[12-(1-deoxynojirimycin)dodecyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 38
  • [ 19130-96-2 ]
  • 28-(2-bromoethyl)corosolic acid ester [ No CAS ]
  • 28-[2-(1-deoxynojirimycin)ethyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 39
  • [ 19130-96-2 ]
  • 28-(2-bromopropyl)corosolic acid ester [ No CAS ]
  • 28-[3-(1-deoxynojirimycin)propyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 40
  • [ 19130-96-2 ]
  • 28-(4-bromobutyl)corosolic acid ester [ No CAS ]
  • 28-[4-(1-deoxynojirimycin)butyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 41
  • [ 19130-96-2 ]
  • 28-(5-bromoamyl)corosolic acid ester [ No CAS ]
  • 28-[5-(1-deoxynojirimycin)amyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 42
  • [ 19130-96-2 ]
  • 28-(6-bromohexyl)corosolic acid ester [ No CAS ]
  • 28-[6-(1-deoxynojirimycin)hexyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 43
  • [ 19130-96-2 ]
  • 28-(8-bromooctyl)corosolic acid ester [ No CAS ]
  • 28-[8-(1-deoxynojirimycin)octyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 44
  • [ 19130-96-2 ]
  • 28-(10-bromodecyl)corosolic acid ester [ No CAS ]
  • 28-[10-(1-deoxynojirimycin)decyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 45
  • [ 19130-96-2 ]
  • 28-(12-bromododecyl)corosolic acid ester [ No CAS ]
  • 28-[12-(1-deoxynojirimycin)dodecyl]corosolic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 46
  • [ 876724-03-7 ]
  • [ 19130-96-2 ]
  • 28-[2-(1-deoxynojirimycin)ethyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 47
  • [ 19130-96-2 ]
  • 3-bromo-prop-1-yl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate [ No CAS ]
  • 28-[3-(1-deoxynojirimycin)propyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 48
  • [ 876724-06-0 ]
  • [ 19130-96-2 ]
  • 28-[4-(1-deoxynojirimycin)butyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 49
  • [ 19130-96-2 ]
  • 28-(5-bromoamyl)maslinic acid ester [ No CAS ]
  • 28-[5-(1-deoxynojirimycin)amyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 50
  • [ 19130-96-2 ]
  • 28-(6-bromohexyl)maslinic acid ester [ No CAS ]
  • 28-[6-(1-deoxynojirimycin)hexyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 51
  • [ 19130-96-2 ]
  • 28-(8-bromooctyl)maslinic acid ester [ No CAS ]
  • 28-[8-(1-deoxynojirimycin)octyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
  • 52
  • [ 19130-96-2 ]
  • 28-(10-bromodecyl)maslinic acid ester [ No CAS ]
  • 28-[10-(1-deoxynojirimycin)decyl]maslinic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere; General procedure: To a solution of compound 2a (1.27 g, 2.19 mmol) anhydrous K2CO3 (251 mg, 6.57 mmol) and 1-deoxynojirimycin (714 mg, 4.38 mmol) in dry dMF (15 mL) which was stirred for 15 min, then added potassium iodide (2.18 g, 12.74 mmol) in a nitrogen atmosphere and left standing overnight at 50 C. The reaction was quenched by 1 N HCl, diluted with water and ethyl acetate, and combined organic layer was dried over anhydrous Na2SO4, concentrated and dried in vacuo. The crude product was chromatographed on silica gel to give a white solid 4a. Yield 52%, mp: 173-174 C. 1 H NMR (400 MHz, dMSO-d6): delta5.19 (s, 1H), 4.76-4.78 (m, 2H), 4.70 (s, 1H), 4.40 (s, 1H), 4.32 (s, 1H), 4.25 (s, 1H), 4.07-4.10 (m, 1H), 3.87-3.90 (m, 1H), 3.77-3.80 (m, 1H), 3.51-3.54 (m, 1H), 3.16-3.20 (m, 1H), 2.89-2.99 (m, 3H), 2.73-2.79 (m, 3H), 2.04-2.11 (m, 2H), 1.90-1.97 (m, 1H), 1.82-1.85 (m, 1H), 1.72-1.75 (m, 1H), 1.56-1.64 (m, 3H), 1.48-1.52 (m, 2H), 1.32-1.41 (m, 5H), 1.23 (s, 3H), 1.07 (s, 3H), 0.90 (d, J = 16 Hz, 12H), 0.68 (s, 3H), 0.63 (s, 3H). 13C NMR (100 MHz, dMSO-d6): delta 177.23, 143.99, 122.48, 82.81, 79.69, 71.30, 69.90, 67.70, 66.92, 61.98, 59.98, 58.16, 55.31, 50.72, 47.62, 47.36, 46.47, 46.04, 41.76, 41.31, 38.19, 33.76, 33.33, 32.77, 32.55, 31.49, 30.91, 29.34, 27.66, 26.27, 23.96, 23.54, 23.09, 22.60, 18.58, 17.65, 17.26, 16.84. HRMS (ESI, m/z): [M +K]+ Calcd for C38H63NKO8: 700.4185; found: 700.4185.
Same Skeleton Products
Historical Records

Similar Product of
[ 19130-96-2 ]

Chemical Structure| 73285-50-4

A198597[ 73285-50-4 ]

(2R,3R,4R,5S)-2-(Hydroxymethyl)piperidine-3,4,5-triol hydrochloride

Reason: Free-salt